5 (More) Truths About Quitting Your Job to Travel the World

So you think you want to quit your job to travel? Sounds amazing. But don’t be fooled—it’s not all motorbike adventures and daiquiris on the beach. Traveling long-term, and embracing the career uncertainty that accompanies it, is no picnic. I would know. In the fall of 2014, I gave up my cushy job as a magazine editor in New York to embark on a year-long excursion with my begrudging boyfriend.

Fast-forward 365 days, and we’ve explored 15 countries and two special administrative regions, including China, Hong Kong, Macau, the Philippines, Thailand, Myanmar, India, Sri Lanka, Singapore, Malaysia, Cambodia, Vietnam, Taiwan, Japan, South Korea, Indonesia, and Australia. I checked in with The M Dash around the six-month mark to report my experience to date—the highs, lows, and dirty little secrets nobody warns you about. Now I’m back in the U.S. and planning my next move. Am I glad I did it? Hell yeah. Would I do it again? In a heartbeat. But that doesn’t mean everyone should. Here, five things to consider before you hand in that two-week notice

Spotted outside Nishiki Market in Kyoto, Japan.

1. Long-term travel is exhausting.

You don’t think about this when you’re sitting in a job you dislike, dreaming of the “what ifs.” But nonstop travel can be physically, mentally, and financially draining. The faster you go and the more you try to see, the tougher it gets. Rootlessness and a lack of routine can be thrilling for some and panic-inducing for others. So before you give up your day-to-day, do a bit of soul-searching and ask yourself: Do I hate not knowing where my next paycheck is coming from? Do I freak out over minor disruptions, like missed trains or delayed flights? Do I agonize over things beyond my control, like typhoons or terrorist attacks? If you answered “yes” to any of those questions, then maybe all you need is a two-month sabbatical, or even a great ten-day vacation. Why rush to the E.R. when a Band-Aid will do?

2. You can’t be a “digital nomad” if you can’t plug in.

Heading into the trip, my grand plan was to save up a bunch of money but also do a bit of writing from the road. What I didn’t anticipate was just how slow and/or non-existent the internet connection would be in the majority of countries we visited—including places I thought were more technologically savvy, like South Korea and Japan. (Don’t even get me started on the Great Firewall of China and its quest to block, oh, everything.) Moreover, traveling itself became a full-time job; when we weren’t busy experiencing a place, we were researching or making bookings. Point being: If you think you’re going to quit your office job for a sweet telecommuting gig, you better make damn sure you know how solid the WiFi hookup is wherever you’re headed. After all, did you really fly to the other side of the world to sit in a Starbucks?

Cruising Bai Tu Long Bay in Northern Vietnam.

3. Nobody cares about your trip. Really.

In my original “Travel Truths” post, my number-one rule was: “Not everyone will be stoked for you.” Well, guess what? If they didn’t want to hear about your travels before you left, they certainly don’t want to hear you start sentences with the phrase, “One time in [fill-in-the-blank country]…” And that sucks. When you return from any kind of extended jag, you’ll feel as if you’ve conquered the world (because you have). You’ll have a million crazy stories and photos to share, but you’ll quickly learn that nobody—not the immigration officer at LAX, not your old work pals, not even your mother—wants to hear or see them. On the contrary, what people do want to know is how you plan to get a job, make money, make up for that year-long gap in your résumé, and get a new apartment now that you’re “back in reality.” Better thicken up that skin, woman—you’re gonna need it.

4. You’ll be depressed when it’s all over.

Unless you had a terrible go of it on the road, there’s just no way around this. Nothing at home could possibly be as stimulating or challenging as the travel you’ve been doing. Every day was an adventure. Back home, you know the count, even if you have no job or routine in place. Compounding that low-grade depression will be catch-up sessions with friends, wherein you learn what they’ve been up to while you gallivanted around the world: winning promotions, landing book deals, buying homes, making babies. This may lead you to ask, “Wow, what have I done with my life?” But you just have to flick that demon off your shoulder and keep your perspective. I’ve always been driven more by experiences than status or material things, and my travels have reinforced that. If I’m never “rich” in the monetary sense, so be it. I saw more of the world in the last year than some people see in a lifetime. You can’t put a price on that.

Chishingtan Beach in Hualien, Taiwan.

5. You might—gasp!—miss office life. Or at least work.

While traveling, I didn’t miss having a structured work environment or even a steady paycheck; but I missed having the ability to contribute creatively to an enterprise larger than myself. I got over it by channeling my passion into a project of my own making. In due time, travel taught me to be fiercer, more independent, and more self-motivated. Most importantly, it gave me the confidence to take even greater risks—like starting my own business. For a hot second, I considered rejoining the cubicle army in New York upon my re-entry, but I now accept that I’m just not cut out for that kind of sedentary and regimented lifestyle. Travel taught me how to make my own opportunities, and that’s exactly what I plan to do now that I’m back.

Photos by Ashlea Halpern

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Ashlea Halpern is the co-founder of Cartogramme and editor-at-large for AFAR Media. She edits New York Magazine's pop-up travel blog, The Urbanist, and writes regularly for Condé Nast Traveler, Bon Appétit, Airbnbmag, and Wired. After spending 3.5 years traveling Asia, Australia, the Arctic, and North America, she has settled in Minneapolis, MN—the most underrated city in the lower 48, bar none. Follow her adventures on Instagram at @ashleahalpern and @cartogramme.
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